- Serena throws Jenny a party for her 16th birthday, but things get out of control when Poppy Lifton turns the small gathering into a huge social event.
- Serena decides to throw Jenny an intimate party for her 16th birthday, but things get out of control when Serena's friend Poppy Lifton, returns and turns the small gathering at the van der Woodsen apartment into a huge social event. Meanwhile, Vanessa agrees to help Chuck with a scheme that will make Blair and Nate jealous... and they end up having sex in the process. Also, Rufus learns that Dan will not receive financial aid at Yale and tries to figure out another way to cover the cost of Dan's education, with which Lily offers to help. Meanwhile, Dan receives a letter from Boston from Rufus and Lily's illegitimate son wanting to meet with him.—matt-282
- JENNY'S KINDA-NOT-SWEET SIXTEEN
Serena (Blake Lively) decides to throw Jenny Humphrey (Taylor Momsen) an intimate party for her sixteenth birthday, but things get out of control when Poppy Lifton (guest star Tamara Feldman) turns a small gathering into a huge social event.
In a moment of weakness, Vanessa (Jessica Szohr) agrees to help Chuck (Ed Westwick) with a scheme having to do with Blair (Leighton Meester) and Nate (Chace Crawford).
Rufus (Matthew Settle) learns that Dan (Penn Badgley) will not receive financial aid at Yale and tries to figure out another way to cover the cost of his education.
Kelly Rutherford also stars. Armie Hammer guest stars as Poppy's boyfriend, Gabriel Serrano. Allison Liddi-Brown directed the episode written by Sarah Frank-Meltzer.
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